1. Field of the Invention
The present invention relates to cyanoenamine derivatives, their process of preparation, intermediate compounds, their use as fungicide active agents, particularly in the form of fungicide compositions, and methods for the control of phytopathogenic fungi, notably of plants and in material protection, using these compounds or compositions.
2. Description of Related Art
In WO 01/85673 arylcyanoenaminones of general formula:
are described, wherein K represents an oxygen or sulphur atom, Ar represents an optionally substituted aryl or heteroaryl, X may represent a cyano group, Z represents an optionally substituted phenyl or naphthyl and Y represents an optionally substituted alkyl chain. However, there is no disclosure or suggestion in this documents of any derivative wherein Ar represents an alkyl-based chain or a heterocycle. Moreover, only herbicidal, acaricidal and insecticidal activities are claimed.
In DE-A 196 49 381 certain UV-A filters of general formula
are described, wherein R1, R2 and R3 represent an hydrogen, an alkyl, a cycloalkyl or can form a ring when connected together, R4 represents an aryl group and R5 represents an aryl or heteroaryl group. However, there is no disclosure or suggestion in this documents of any derivative wherein R5 is a substituted alkyl group nor a substituted arylalkyl or heteroarylalkyl group and no disclosure is made of any biological utility.
In CN101544669A aminophosphonates containing a phenylcyanopropenoate group of general formula
are described. The use of these compounds as plant antiviral agent is claimed. However, there is no disclosure or suggestion in this documents of any derivative without the phosphonate moiety.
In WO 2008/081711 (EP-A 2 105 434) certain 2-fluorinated acyl-3-aminoacrylonitriles of general formula
are described, wherein R1 and R2 can represent a C1-C6 alkyl, a C3-C6 cycloalkyl, an aryl or an arylalkyl, R3 can represent an optionally substituted aryl group and Rf is limited to represent a C1-C6 alkyl group which is substituted by at least one fluorine atom. However, there is no disclosure or suggestion in this documents of any derivative wherein Rf does not represent a fluorinated C1-C6 alkyl group and no disclosure is made of any biological utility. JP-A 2009-215194 and WO 2008/102678 (EP-A 2 128 139) also claim the use of these compounds as synthesis intermediates towards pyrazoles with the same restrictions on Rf.
Certain 3-(pyridin-2-ylamino)acrylonitriles as synthesis intermediates towards pyrido[1,2-a]pyrimidines are described in Synthesis, 1982, 9, 791-792. However limitation is made to benzoyl analogs and only 2-benzoyl-3-phenyl-3-(pyridin-2-ylamino)acrylonitrile is prepared with no disclosure of biological utility. Certain α-oxobutenamides can be obtained by opening of 1H-pyrrole-2,3-diones (see Liebigs Ann. 1995, 537-543). In the course of this study 4-anilino-3-cyano-2-oxo-N,4-diphenylbut-3-enamide and 4-anilino-3-cyano-N-cyclohexyl-2-oxo-4-phenylbut-3-enamide are prepared with no disclosure of biological activity. A methods to prepare certain β-enaminoketones is described in Synthetic Commun. 1986, 16, 673-680. In the course of this study 2-benzoyl-3-(ethylamino)-3-phenylacrylonitrile is prepared with no disclosure of biological activity.
JP-A 06-214339 describes certain compounds used as photochromic materials of general formula
wherein R1 could represent a cyano group, R2 could represent a substituted amino group and Ar represents an aryl group. However, there is no disclosure or suggestion in this documents of any derivative wherein Ar is different from an aryl group and no disclosure is made of any biological utility. Certain cyanoenaminones used as bidentates ligands for catalysis are described in (Eur. J. Org. Chem. 2008, 4139-4147). In the course of this study 4,4,5,5,6,6,6-heptafluoro-2-{[(4-methylphenyl)amino](phenyl)methylene}-3-oxohexanenitrile has been prepared with no disclosure of biological activity. EP-A 0 990 664 discloses further ligands for catalysts which may have an enamine structure. Biological activity is not described. The compounds disclosed in these documents do not prove to provide a comparable utility than the compounds according to the invention.
Since the ecological and economical demands made on modern active compounds, for example fungicides, are increasing constantly, for example with respect to activity spectrum, toxicity, selectivity, application rate, formation of residues and favorable manufacture, and there can furthermore be problems, for example, with resistance, there is a constant need to develop novel fungicides which, at least in some areas, have advantages over those of the prior art. Surprisingly, it has now been found that cyanoenamines of the formula (I) (see below) are suitable as fungicides and, at least in some aspects, have improved properties compared to known fungicidally active compounds.